Stephanie Shepard: From Courtroom Shock to Advocacy for Justice

Sometimes the scariest moment isn’t when the prison doors close behind you—it’s when you realize, five years in, that this isn’t a mistake and no one is coming to save you.

I met Stephanie Shepard through my friend Seth Ferranti, and when he told me I had to talk to her, I knew there was something special about her story. What I didn’t expect was how her journey would hit me right in the chest—from a suburban real estate agent to serving nine years of a ten-year federal sentence for cannabis conspiracy, to becoming a fierce advocate for justice reform.

From Buzzer to Federal Warrant in 24 Hours

Stephanie grew up as the youngest of seven kids in what she calls a typical family. Her dad was born in 1919, cannabis wasn’t part of their world, and she didn’t even try it until she was 28. She was selling real estate in New York, living her life, when an ex-boyfriend got arrested for cannabis charges.

The nightmare began with what seemed like a simple favor. When his lawyer asked if she’d let him stay at her place during medical bond, she said yes. Standing in that courtroom, she heard the judge say something that changed everything: “I find this young lady responsible and I’m going to recommend he be released to her custody.”

The very next day, as she was getting ready to pick him up, her buzzer rang. Two agents were at her door with a warrant for her arrest.

“I never really believed that me would be getting into any serious trouble behind cannabis,” Stephanie told me. “At the most, I thought you know what can happen—a fine, maybe some type of probation. I just wasn’t believing it.”

When 120 Months Doesn’t Compute

After a year on pretrial, losing her real estate license, and weekly drug testing, Stephanie found herself back in that courtroom. When the judge announced her sentence—120 months—she didn’t even know what that meant.

“I don’t normally talk in months so I don’t know the month calculations,” she explained. But her sister who flew in from California knew exactly what it meant. “When they announced the amount of time, I just remember my sister screaming, just screaming. And I just turned to her and I wanted her to feel better, so I smiled. ‘It’s okay, we’ll be okay. We’ll work it out. It’s fine, calm down’ and I’m smiling. And they take me back behind the doors and that’s when I screamed.”

Ten years. A entire decade.

The Five-Year Reality Check

It took Stephanie five years—half her sentence—to truly accept that this was her reality. “I almost had like a Karen-ish way about me. You know, ‘I want to speak to your supervisor.’ I didn’t even realize that this is serious,” she laughed, remembering her first days at MDC Brooklyn.

She was transferred five different times, teaching ESL classes to earn $80 a month, refusing to work in the factory-like Unicor program. She was determined not to lose herself in the system. Teaching gave her purpose, an office where she could be alone, and the closest thing to her outside life she could find.

The transfers were brutal—flying commercial while in custody, going through Oklahoma’s transfer center, ending up in Phoenix where it hit 120 degrees with no air conditioning. When her father got sick, she requested to see him in the hospital. It took them a week to approve it. He died that morning.

“They told me, ‘Well if you go see him in the hospital, you’re not going to be able to go to the funeral.’ And I said, ‘I don’t want to go to a funeral. I want to go see my father alive,’” she remembered.

Fighting for Those Still Inside

Today, Stephanie works full-time for the Last Prisoner Project, using everything she learned during those nine years to help others still trapped by cannabis convictions. They provide re-entry grants, match people with pro bono attorneys, and push for policy changes. While people walk into dispensaries freely, spending billions in a legal industry, there are still people serving decades for the same plant.

“After everything that I’ve been through, the biggest takeaway would have to be that it’s not over,” Stephanie told me as we wrapped up. “It’s not over until these people who are sitting where I was sitting just three short years ago are home and moving on with their life the way I’m trying to do today.”

Her story reminds me why these conversations matter. Behind every statistic about mass incarceration is a human being—someone’s daughter, someone’s sister—whose life got turned upside down. Stephanie didn’t just survive her nightmare; she’s using it to make sure fewer people have to live through what she did.

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